US4515626AExpiredUtility

N-(Cyclopropyl-triazinyl-n'-(arylsulfonyl) ureas having herbicidal activity

92
Assignee: CIBA GEIGY CORPPriority: Oct 6, 1982Filed: Sep 26, 1983Granted: May 7, 1985
Est. expiryOct 6, 2002(expired)· nominal 20-yr term from priority
Inventors:Henry Szczepanski
C07D 251/18C07D 251/22C07D 521/00C07D 251/20C07D 239/42C07D 251/16A01N 47/36C07C 45/455C07D 251/24
92
PatentIndex Score
18
Cited by
4
References
13
Claims

Abstract

N-(Cyclopropyl-triazinyl- and -pyrimidinyl)-N'-arylsulfonyl ureas of the formula ##STR1## wherein Ar is a phenyl group ##STR2## or a naphthyl group ##STR3## and Q is a group X-A or R 3 , A is a C 3 -C 6 -alkynyl group, a C 1 -C 6 -alkyl group which is unsubstituted or substituted by halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl or C 1 -C 4 -haloalkylsulfonyl, or a C 2 -C 6 -alkenyl group which is unsubstituted or substituted by the groups given in the foregoing for C 1 -C 6 -alkyl, or A is a phenyl or benzyl group, E is the methine group or nitrogen, X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge, Z is oxygen or sulfur, R 1 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, R 2 is halogen, C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, amino, C 1 -C 3 -alkylamino, di-(C 1 -C 3 -alkyl)amino, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkoxyalkyl, R 3 is hydrogen, halogen, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl, C 1 -C 4 -haloalkyl, or a group --X-R 6 , --COZR 11 , --NO 2 or --CO-NR 8 R 9 , --CN, --COR 10 , --NR 1 R 7 or --NR 1 -COR 12 , R 4 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, halogen, or alkoxyalkyl having at most 4 carbon atoms, R 5 is the same as R 3 but independent thereof, R 6 and R 7 are each C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl or C 2 -C 6 -alkynyl, R 8 and R 9 independently of one another are each hydrogen, C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl or C 2 -C 6 -alkynyl, R 10 is hydrogen, C 1 -C 4 -alkyl or C 1 -C 3 -haloalkyl, R 11 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 5 -alkenyl, C 3 -C 5 -alkynyl, phenyl or benzyl, and R 12 is the same as R 1 but independent thereof, and the salts of these compounds with amines, alkali metal bases or alkaline-earth metal bases or with quaternary ammonium bases, have good pre- and post-emergence-selective herbicidal and plant-growth-regulating properties.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. An N-(cyclopropyl-triazinyl-)-N'-(arylsulfonyl)urea of the formula I ##STR21## wherein Ar is a phenyl group ##STR22## or a naphthyl group ##STR23## and Q is a group X-A or R 3 , A is a C 3  -C 6  -alkynyl group, a C 1  -C 6  -alkyl group which is unsubstituted or substituted by halogen, C 1  -C 4  -alkoxy, C 1  -C 4  -alkylthio, C 1  -C 4  -alkylsulfinyl, C 1  -C 4  -alkylsulfonyl, C 1  -C 4  -haloalkoxy, C 1  -C 4  -haloalkylthio, C 1  -C 4  -haloalkylsulfinyl or C 1  -C 4  -haloalkylsulfonyl, or a C 2  -C 6  -alkenyl group which is unsubstituted or substituted by the groups given in the foregoing for C 1  -C 6  -alkyl, or A is a phenyl or benzyl group,   X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge,   Z is oxygen or sulfur,   R 1  is hydrogen, C 1  -C 4  -alkyl or C 1  -C 4  -alkoxy,   R 2  is halogen, C 1  -C 3  -alkyl, C 1  -C 3  -haloalkyl, C 1  -C 3  -alkoxy, C 1  -C 3  -haloalkoxy, amino, C 1  -C 3  -alkylamino, di-(C 1  -C 3  -alkyl)amino, C 3  -C 6  -cycloalkyl or C 2  -C 6  -alkoxyalkyl,   R 3  is hydrogen, halogen, C 1  -C 5  -alkyl, C 2  -C 5  -alkenyl, C 1  -C 4  -haloalkyl, or a group --X--R 6 , --COZR 11 , --NO 2  or --CO--NR 8  R 9 , --CN, --COR 10 , --NR 1  R 7  or --NR 1  --COR 12 ,   R 4  is hydrogen; C 1  -C 4  -alkyl, C 1  -C 4  -alkoxy, C 1  -C 4  -alkylthio, C 1  -C 4  -haloalkyl, C 1  -C 4  -haloalkoxy, halogen, or alkoxyalkyl having at most 4 carbon atoms,   R 5  is the same as R 3  but independent thereof,   R 6  and R 7  are each C 1  -C 5  -alkyl, C 2  -C 5  -alkenyl or C 2  -C 6  -alkynyl,   R 8  and R 9  independently of one another are each hydrogen, C 1  -C 5  -alkyl, C 2  -C 5  -alkenyl or C 2  -C 6  -alkynyl,   R 10  is hydrogen, C 1  -C 4  -alkyl or C 1  -C 3  -haloalkyl,   R 11  is hydrogen, C 1  -C 4  -alkyl, C 1  -C 3  -haloalkyl, C 3  -C 5  -alkenyl, C 3  -C 5  -alkynyl, phenyl or benzyl, and   R 12  is the same as R 1  but independent thereof.   
     
     
       2. A compound according to claim 1, wherein Z is oxygen. 
     
     
       3. A compound of the formula I according to claim 2, wherein Ar is a phenyl group substituted in the orthoposition by Q, R 1  is hydrogen or methyl, and R 2  is a C 1  -C 3  -alkyl, C 1  -C 3  -haloalkyl, C 1  -C 3  -alkoxy, C 1  -C 3  -haloalkoxy or C 1  -C 3  -alkylamino group. 
     
     
       4. A compound of the formula I according to claim 3, wherein Ar is a phenyl group substituted in the orthoposition by C 1  -C 4  -alkoxycarbonyl. 
     
     
       5. A compound of the formula I according to claim 3, wherein Ar is a phenyl group substituted in the orthoposition by C 1  -C 3  -haloalkoxy. 
     
     
       6. A compound of the formula I according to claim 3, wherein Ar is a phenyl group substituted in the orthoposition by halogen or nitro. 
     
     
       7. N-(4-Cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)-N'-(2-methoxycarbonylbenzenesulfonyl)urea according to claim 4. 
     
     
       8. N-(4-Cyclopropyl-6-ethoxy-1,3,5-triazin-2-yl)-N'-(2-difluoromethoxybenzenesulfonyl)urea according to claim 5. 
     
     
       9. A herbicidal and plant-growth-reducing composition which contains, as active ingredient, an effective amount of an N-phenylsulfonyl-N'-triazinyl-urea according to claim 1, together with a carrier. 
     
     
       10. A method of controlling undesirable plant growth, which method comprises applying thereto or to the locus thereof an effective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea according to claim 1. 
     
     
       11. A method of reducing plant growth, which method comprises applying thereto or to the locus thereof an effective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea according to claim 1. 
     
     
       12. A method for the pre- or post-emergence controlling of weeds in crops of cultivated plants, which method comprises applying thereto or to the locus thereof an effective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea according to claim 1. 
     
     
       13. A method of suppressing plant growth beyond the two-leaf stage, which method comprises applying before emergence of the plants an effective amount of an N-(cyclopropyl-triazinyl)-N'-(arylsulfonyl)-urea according to claim 1.

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